US20130184346A1 - Oil and fat composition - Google Patents

Oil and fat composition Download PDF

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Publication number
US20130184346A1
US20130184346A1 US13/823,403 US201113823403A US2013184346A1 US 20130184346 A1 US20130184346 A1 US 20130184346A1 US 201113823403 A US201113823403 A US 201113823403A US 2013184346 A1 US2013184346 A1 US 2013184346A1
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Prior art keywords
fat
fatty acids
oil
mass
oil composition
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US13/823,403
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English (en)
Inventor
Katsuyoshi Saito
Yuki Mitsui
Junya Moriwaki
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Kao Corp
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Kao Corp
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Assigned to KAO CORPORATION reassignment KAO CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MITSUI, YUKI, MORIWAKI, JUNYA, SAITO, KATSUYOSHI
Publication of US20130184346A1 publication Critical patent/US20130184346A1/en
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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013—Other fatty acid esters, e.g. phosphatides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A61K31/231—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having one or two double bonds

Definitions

  • the present invention relates to a fat or oil composition containing diacylglycerol.
  • diacylglycerol has an effect of improving a blood cholesterol level (see Patent Document 1) and has an effect of reducing accumulation of body fat, thereby preventing obesity (see Patent Document 2). This is probably because an intake of the diacylglycerol contributes to inhibiting an increase in a postprandial blood neutral fat level. On the other hand, the diacylglycerol is liable to crystallize under low temperature because of having a higher melting point than triacylglycerol.
  • a method using a polyglycerin fatty acid ester is known as a method of inhibiting crystallization of a fat or oil at low cost.
  • a method using a polyglycerin fatty acid ester having an average polymerization degree of glycerin of from 2 to 15 and containing unsaturated fatty acids at 4 mass % or less in its constituent fatty acids see Patent Document 3
  • a method using a polyglycerin fatty acid ester having an average polymerization degree of glycerin of from 2 to 15 and containing erucic acid as a main component in its constituent fatty acids see Patent Document 4
  • a method using an esterified product of polyglycerin and fatty acids the esterified product having a hydroxyl value of 100 mg KOH/g or less and the polyglycerin having a hydroxyl value of 850 mg KOH/g or less and having a content of a primary hydroxyl group of 50% or more
  • Patent Document 5 a method using an esterified
  • the present invention relates to the following items (1) to (31). Regarding the embodiment as mentioned below, the present invention also includes other embodiments described below, related to the composition.
  • (a-3) from 0 to 80 mass % of unsaturated fatty acids having 16 or more carbon atoms.
  • (a-3) from 0 to 80 mass % of unsaturated fatty acids having 16 or more carbon atoms.
  • (a-3) from 0 to 70 mass % of unsaturated fatty acids having 16 or more carbon atoms.
  • (a-3) from 0 to 60 mass % of unsaturated fatty acids having 16 or more carbon atoms.
  • (a-3) from 20 to 60 mass % of unsaturated fatty acids having 16 or more carbon atoms.
  • (a-3) from 25 to 40 mass % of unsaturated fatty acids having 16 or more carbon atoms.
  • the present invention provides a diacylglycerol-containing fat or oil composition whose crystallization is inhibited even under low temperature.
  • the inventors of the present invention have made intensive studies to solve the above-mentioned problem. As a result, the inventors found that a polyglycerin fatty acid ester having an average polymerization degree of glycerin of 20 or more exerts an excellent crystallization-inhibiting effect on diacylglycerol, thus improving the low temperature resistance of the diacylglycerol-containing fat or oil composition.
  • a diacylglycerol-containing fat or oil composition whose crystallization is inhibited under low temperature irrespective of the content of diacylglycerol.
  • a polyglycerin fatty acid ester which serves as a component (A) to be used for the fat or oil composition of the present invention, is obtained by esterifying polyglycerin and fatty acids.
  • the polyglycerin fatty acid ester has an average polymerization degree of glycerin of 20 or more, preferably from 20 to 45, more preferably from 25 to 45, more preferably from 25 to 40, more preferably from 30 to 40, even more preferably 31 to 45, from the standpoint of inhibiting the crystallization of diacylglycerol (hereinafter, also referred to as “DAG”) and favorably maintaining the outer appearance of the fat or oil composition containing the diacylglycerol.
  • DAG diacylglycerol
  • the term “average polymerization degree of glycerin” refers to a value obtained by measurement by GPC of the polymerization degree of the polyglycerin part of a polyglycerin fatty acid ester.
  • the constituent fatty acids of the polyglycerin fatty acid ester include (a-1) saturated fatty acids having 16 or more carbon atoms at preferably from 20 to 80 mass (hereinafter, simply described as “%”) of the total amount of the fatty acids, more preferably from 20 to 70%, more preferably from 20 to 60%, more preferably from 25 to 50%, even more preferably from 30 to 45%, from the standpoint of inhibiting the crystallization of diacylglycerol and favorably maintaining the outer appearance.
  • the constituent fatty acids of the polyglycerin fatty acid ester include (a-2) saturated fatty acids having 14 or less carbon atoms at preferably from 0 to 80% of the total amount of the fatty acids, more preferably from 0 to 40%, more preferably from 0 to 38%, more preferably from 10 to 60%, more preferably from 10 to 38%, even more preferably from 20 to 35%, from the standpoint of inhibiting the crystallization of diacylglycerol and favorably maintaining the outer appearance.
  • the constituent fatty acids of the polyglycerin fatty acid ester include (a-3) unsaturated fatty acids having 16 or more carbon atoms at preferably from 0 to 80% of the total amount of the fatty acids, more preferably from 0 to 70%, more preferably from 0 to 60%, more preferably from 20 to 60%, more preferably from 25 to 50%, even more preferably from 25 to 40%, from the standpoint of inhibiting the crystallization of diacylglycerol and favorably maintaining the outer appearance.
  • the constituent fatty acids of the polyglycerin fatty acid ester preferably include (a-1) the saturated fatty acids having 16 or more carbon atoms at from 20 to 80% of the total amount of the fatty acids, (a-2) the saturated fatty acids having 14 or less carbon atoms at from 0 to 80% of the total amount of the fatty acids, and (a-3) the unsaturated fatty acids having 16 or more carbon atoms at from 0 to 80% of the total amount of the fatty acids, more preferably include the saturated fatty acids having 16 or more carbon atoms at from 20 to 80% of the total amount of the fatty acids, the saturated fatty acids having 14 or less carbon atoms at from 0 to 40% of the total amount of the fatty acids, and the unsaturated fatty acids having 16 or more carbon atoms at from 0 to 80% of the total amount of the fatty acids, more preferably include the saturated fatty acids having 16 or more carbon atoms at from 20 to 80% of the total amount of the fatty acids,
  • saturated fatty acids having 16 or more carbon atoms saturated fatty acids having from 16 to 22 carbon atoms are preferred, and palmitic acid and stearic acid are more preferred.
  • saturated fatty acids having 14 or less carbon atoms saturated fatty acids having from 6 to 14 carbon atoms are preferred, and capric acid, lauric acid, and myristic acid are more preferred.
  • unsaturated fatty acids having 16 or more carbon atoms unsaturated fatty acids having from 16 to 22 carbon atoms are preferred, and examples thereof include oleic acid, linoleic acid, and erucic acid. Of those, oleic acid is preferred.
  • the constituent fatty acids of the polyglycerin fatty acid ester may be a single kind of fatty acid or may be a mixture of two or more kinds of fatty acids.
  • the polyglycerin fatty acid ester in the present invention has a hydroxyl value of preferably 80 mg-KOH/g or less, more preferably from 0 to 60 mg-KOH/g, more preferably from 3 to 50 mg-KOH/g, more preferably from 5 to 30 mg-KOH/g, even more preferably from 5 to 20 mg-KOH/g, from the standpoint of inhibiting the crystallization of diacylglycerol and favorably maintaining the outer appearance.
  • the hydroxyl value in the present invention refers to a value obtained by measurement in accordance with Standard Methods for the Analysis of Fats, Oils and Related Materials described in Examples.
  • the content of the polyglycerin fatty acid ester in the fat or oil composition is preferably 0.001% or more, more preferably 0.005% or more, more preferably 0.01% or more, more preferably 0.03% or more, more preferably 0.05% or more, even more preferably 0.1% or more, from the standpoint of inhibiting the crystallization of diacylglycerol. Further, the content of the polyglycerin fatty acid ester in the fat or oil composition is, from the standpoint of its taste and flavor, preferably 5% or less, more preferably 1% or less, more preferably 0.5% or less, even more preferably 0.3% or less.
  • the content of the polyglycerin fatty acid ester in the fat or oil composition is preferably from 0.001 to 5%, more preferably from 0.005 to 5%, more preferably from 0.01 to 1%, more preferably from 0.03 to 1%, more preferably from 0.05 to 0.5%, even more preferably from 0.1 to 0.3%, from the standpoints of the inhibition of the crystallization of diacylglycerol, the taste and flavor, and cookability.
  • Two or more of polyglycerin fatty acid esters may be used in combination.
  • the fat or oil composition of the present invention contains a fat or oil.
  • the “fat or oil” in the present invention includes one or more of glycerols including triacylglycerol, diacylglycerol, and monoacylglycerol.
  • the content of the fat or oil in the present invention is preferably 85% or more in the fat or oil composition of the present invention, more preferably from 90 to 99.999%, more preferably from 95 to 99.5%, even more preferably from 97 to 99%, from the standpoints of physiological effects, industrial productivity, and the outer appearance.
  • the fat or oil composition of the present invention contains diacylglycerol as a component (B) at 20% or more, and contains diacylglycerol at preferably 25% or more, more preferably 30% or more, from the standpoint of the physiological effects. Further, the content of diacylglycerol as the component (B) in the fat or oil composition of the present invention is preferably 99.5% or less, more preferably 98% or less, even more preferably 95% or less, from the standpoint of improving the industrial productivity.
  • the content of diacylglycerol as the component (B) in the fat or oil composition of the present invention is preferably from 20 to 99.5%, more preferably from 25 to 98%, even more preferably from 30 to 95%, from the standpoints of the outer appearance, the industrial productivity, and the physiological effects.
  • the fat or oil composition of the present invention contains triacylglycerol at preferably from 1 to 80%, more preferably from 5 to 80%, even more preferably from 10 to 80%, from the standpoints of the physiological effects, the industrial productivity, and the outer appearance.
  • the content of monoacylglycerol is preferably 2% or less, more preferably from 0.01 to 1.5%
  • the content of a free fatty acid (salt) is preferably 3.5% or less, more preferably from 0.01 to 1.5%, from the standpoint of the taste and flavor or the like.
  • the constituent fatty acids of the triacylglycerol and the monoacylglycerol are preferably the same constituent fatty acids as those of the diacylglycerol from the standpoints of improving the physiological effects and the industrial productivity of the fat or oil composition.
  • the content of an unsaturated fatty acid in the constituent fatty acids of the diacylglycerol is preferably from 80 to 100%, more preferably from 85 to 99%, even more preferably from 90 to 98%, from the standpoints of the outer appearance and the physiological effects.
  • the unsaturated fatty acid has preferably from 14 to 24 carbon atoms, more preferably from 16 to 22 carbon atoms, from the standpoint of the physiological effects.
  • the content of oleic acid in the constituent fatty acids of the diacylglycerol is preferably from 30 to 90%, more preferably from 40 to 80%, more preferably from 45 to 75%, more preferably from 55 to 75%, evenmore preferably from 60 to 75%, from the standpoint of effectively exerting the effects of the present invention, thus improving the outer appearance and the taste and flavor, and the physiological effects.
  • the content of a trans-unsaturated fatty acid in the constituent fatty acids of the diacylglycerol is preferably from 0.01 to 5%, more preferably from 0.01 to 3.5%, even more preferably from 0.01 to 3%, from the standpoints of the physiological effects and the outer appearance. Further, the content of fatty acids having 12 or less carbon atoms is preferably 5% or less, more preferably from 0 to 2%, even more preferably from 0 to 1%, from the standpoint of the taste and flavor.
  • a fat or oil containing diacylglycerol maybe originated from any of a vegetable fat or oil and an animal fat or oil.
  • rapeseed oil sunflower oil
  • corn oil soybean oil
  • linseed oil rice oil
  • safflower oil cottonseed oil
  • palm oil coconut oil
  • olive oil grapeseed oil
  • abocado oil sesame oil
  • peanut oil macadamia nut oil, hazelnut oil, walnut oil, lard, beef tallow, chicken oil, butter oil, fish oil, or the like.
  • a fat or oil prepared by fractionating and mixing these oils and fats or a fat or oil prepared by adjusting a composition of the fatty acid of any of these oils and fats through a hydrogenation, a transesterification reaction, or the like.
  • a nonhydrogenated fat or oil is preferred from the standpoint of reducing the content of a trans-unsaturated fatty acid in all the constituent fatty acids of the resultant fat or oil.
  • the fat or oil containing diacylglycerol may be obtained by an esterification reaction between fatty acids derived from any of the above-mentioned oils and fats and glycerin, a transesterification reaction (glycerolysis) between a fat or oil and glycerin, or the like.
  • These reactions may be carried out by a chemical reaction using an alkali catalyst or the like, and are preferably carried out under an enzymatically mild condition by using a 1,3-selective lipase or the like, from the standpoint of, for example, the taste and flavor.
  • the fat or oil composition of the present invention preferably contains an antioxidant.
  • the content of the antioxidant in the fat or oil composition is preferably from 0.005 to 0.5%, more preferably from 0.04 to 0.25%, even more preferably from 0.08 to 0.2%, from the standpoints of, for example, its taste and flavor, oxidation stability, and suppression of coloration.
  • Any antioxidant which is usually used in a food may be used as the antioxidant. It is possible to use, for example, vitamin E, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), t-butylhydroxyquinone (TBHQ), vitamin C or a derivative thereof, phospholipids, and natural antioxidants such as a rosemary extract.
  • the fat or oil composition of the present invention preferably contains a phytosterol.
  • the content of the phytosterol in the fat or oil composition is preferably from 0.05 to 5%, more preferably from 0.3 to 4.7%, from the standpoints of a cholesterol-lowering effect and the outer appearance.
  • examples of the phytosterol include free forms of ⁇ -sitosterol, ⁇ -sitosterol, stigmasterol, campesterol, ⁇ -sitostanol, ⁇ -sitostanol, stigmastanol, campestanol, cycloartol, or the like, and ester forms such as fatty acid esters thereof.
  • the fat or oil composition of the present invention has the excellent property in term of outer appearance, workability, taste and flavor, or the like.
  • the fat or oil composition can be used in the same way as a general edible fat or oil, and can be applied to various beverages and foods each produced by using a fat or oil.
  • the foods and beverages include a health food, a functional food and a food for specified health use or the like, for aiming at promotion of good health by exerting an anti-obesity function.
  • Specific examples of the products include: bakery foods such as breads, cakes, cookies, pies, pizza crusts, and bakery mixes; oil-in-water type emulsions such as soup, sauce, dressing, mayonnaise, coffee cream (including powder form), ice cream, and whipped cream; water-in-oil type emulsions such as margarine, spread, and buttercream; snack foods such as potato chips; milk products such as chocolate, caramel, cheese, and yoghurt; and dough, enrober oils and fats, filling oils and fats, noodles, frozen foods, retort foods, beverages and roux or the like.
  • the polyglycerin fatty acid ester having an average polymerization degree of glycerin of 20 or more is added to the fat or oil containing diacylglycerol to exert an excellent crystallization-inhibiting effect on the diacylglycerol, thus improving the low temperature resistance of the fat or oil composition containing diacylglycerol at a high content.
  • A Amount (ml)) of a 0.5 mol/L potassium hydroxide-ethanol reference solution used in a blank test
  • B Amount (ml) of a 0.5 mol/L potassium hydroxide-ethanol reference solution used in a main test
  • F1 Factor of a 0.5 mol/L potassium hydroxide-ethanol reference solution
  • C Collection amount (g) of a sample)
  • the solution was subjected to titration with a 0.1 mol/L potassium hydroxide-ethanol reference solution by using a phenolphthalein indicator, and a value calculated from the results of the titration on the basis of the following equation was defined as “acid value (mg-KOH/g).”
  • a polyglycerin fatty acid ester was separated into a polyglycerin part and a fatty acid part in accordance with a method described in “Polyglycerin ester (p. 75) ” issued by Sakamoto Yakuhin Kogyo Co., Ltd.
  • the resultant polyglycerin part was used for the analysis of the average polymerization degree of glycerin and the resultant fatty acid part was used for the analysis of the constituent fatty acids of the polyglycerin fatty acid ester.
  • the polyglycerin was analyzed by GPC under the conditions of using TSK 2500 PWXL (TOSOH CORPORATION) as a column, using distilled water (in which trifluoroacetic acid was added at 0.1%) as a solvent, setting the flow rate to 1 mL/min, using RID as a detector, setting the temperature to 40° C., and setting the injection volume to 50 ⁇ L.
  • a standard curve was prepared by using polyethylene glycol, to thereby measure the weight-average molecular weight (Mw2) of the polyglycerin in terms of polyethylene glycol and the molecular weight (Mw1) of glycerin. Subsequently, the conversion factor (F) of glycerin was calculated on the basis of the following equation (1).
  • the “average polymerization degree of glycerin” in the polyglycerin was calculated by using the weight-average molecular weight (Mw2) calculated as described above in the following equation (2).
  • n (Mw2 ⁇ F ⁇ 18)/74 (2)
  • n represents the weight-average polymerization degree of glycerin
  • F represents the conversion factor of glycerin
  • Mw2 represents the weight-average molecular weight of polyglycerin.
  • composition of the constituent fatty acids of each polyglycerin fatty acid ester was measured by the same method as the composition of the constituent fatty acids of each fat or oil.
  • Rapeseed oil was hydrolyzed, yielding fatty acids. 564 g of the fatty acids and 92 g of glycerin were mixed, and the mixture was subjected to an esterification reaction by using an immobilized 1,3-selective lipase (manufactured by Novo Nordisk Pharmaceutical Industries, Inc.) as a catalyst. After the lipase preparation was filtered off, the product after completion of the reaction was subjected to molecular distillation, followed by decoloration, water washing, and deodorization at 235° C. for 1 hour, thereby yielding a fat or oil X.
  • an immobilized 1,3-selective lipase manufactured by Novo Nordisk Pharmaceutical Industries, Inc.
  • Rapeseed oil was added to the fat or oil X to adjust the content of DAG, thereby yielding oils and fats Y and Z.
  • Soybean oil was hydrolyzed, yielding fatty acids, followed by wintering, thereby reducing the amount of saturated fatty acids therein.
  • 395 g of the resultant fatty acids, 169 g of fatty acids obtained by hydrolyzing rapeseed oil, and 92 g of glycerin were mixed, and the mixture was subjected to an esterification reaction by using an immobilized 1,3-selective lipase (manufactured by Novo Nordisk Pharmaceutical Industries, Inc.) as a catalyst. After the lipase preparation was filtered off, the product after completion of the reaction was subjected to molecular distillation, followed by decoloration, water washing, and deodorization at 215° C. for 1 hour, thereby yielding a fat or oil W.
  • an immobilized 1,3-selective lipase manufactured by Novo Nordisk Pharmaceutical Industries, Inc.
  • Rapeseed oil was hydrolyzed, yielding fatty acids.
  • 2,500 g of the fatty acids and 410 g of glycerin were mixed, and the mixture was subjected to an esterification reaction by using an immobilized 1,3-selective lipase (manufactured by Novo Nordisk Pharmaceutical Industries, Inc.) as a catalyst.
  • an immobilized 1,3-selective lipase manufactured by Novo Nordisk Pharmaceutical Industries, Inc.
  • the product after completion of the reaction was subjected to molecular distillation, followed by decoloration, water washing, and deodorization at 235° C. for 1 hour, thereby yielding a fat or oil V.
  • Table 2 shows the compositions of glyceride and the compositions of fatty acid in the resultant oils and fats X, Y, Z, W, and V.
  • PGE 1, PGE 4, PGE 7, PGE 8, PGE 10, or PGE 11 was added to the DAG-containing fat or oil V so as to achieve the various concentrations shown in Table 7, thereby preparing DAG-containing fat or oil compositions of Examples 15 to 22 and Comparative Examples 17 and 18.
  • each of these fat or oil compositions was poured in a 30-gram aliquot into a glass vial (SV-50 manufactured by Niommen-Rika Glass Co., Ltd.). The glass vial was closed with a lid, and left to stand still for 1 to 7 days in a refrigerator at 5° C. (in the cases of Examples 1 to 5 and Comparative Examples 1 to 4 each prepared by using the fat or oil X), a refrigerator at 0° C. (in the cases of Examples 6 to 14 and Comparative Examples 5 to 16 each prepared by using the fat or oil Y, Z, or W), or a refrigerator at 8° C. (in the cases of Examples 15 to 22 and Comparative Examples 17 and 18 each prepared by using the fat or oil V). The presence or absence of crystals was checked visually every day on the basis of the criteria shown below. The results are shown in Tables 3 to 7.
  • Example 10 Example 11
  • Example 12 9
  • 10 11 Fat or oil Fat or oil Z Fat or oil Z Fat or oil Z Fat or oil Z Fat or Fat or Oil Z Oil Z oil Z oil Z Added PGE Free of PGE PGE 1 PGE 2 THL-15 PGE 3 PGE 4 PGE 5 Num- First 3 4 4 4 4 4 ber day of Second 3 3 3 4 4 4 ob- day serva- Third 3 3 3 3 4 4 4 tion day days Fourth 3 3 3 3 4 4 4 (0° C.) day Fifth 3 3 3 3 4 4 4 day

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JP5872217B2 (ja) 2016-03-01
JP2012082402A (ja) 2012-04-26
TW201210512A (en) 2012-03-16
EP2617292A4 (en) 2014-08-06
WO2012036145A1 (ja) 2012-03-22

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